I once did NYC to Stowe, VT and back in one day and it was not even Iron Butt or a bet deal. I took all local roads and few detours on my way north anticipating good overnight rest ahead.  But as soon as I got to Stowe I received a call from work (emergency) and had to turn around and rush back to NYC. Bike’s trip meter clocked me with ~800 miles that day. My backside almost fell off. 

What was your longest or toughest one day ride?

Ride safe!
Alex

>1100 miles from Tampa, FL to Ft Smith, OK (non-stop 'cept for gas) on day one of a month long trip. The scorching July heat, not the miles, made it tough =)

Port Orchard WA to Ft Irwin, CA, 1186 miles.  Never wear bicycle shorts on a long trip.  Taught for a week and repeated trip back, shaved over an hour off the return trip.  The return trip was much, much better.  I still have scars from the trip down, I'd post pics but this is a family oriented forum

People can't seem to understand us, we eat miles 

My longest single day was Austin TX to Colorado Springs, CO, almost 900 miles. But I think my hardest day was last summer Fayetteville AR to Clayton NM. Only 650 or so but it was HOT!! 105+ and windy. 12 hours riding in a hair dryer in a straight line with the totally uninspired scenery of Oklahoma.

>1100 miles from Tampa, FL to Ft Smith, OK (non-stop 'cept for gas) on day one of a month long trip. The scorching July heat, not the miles, made it tough =)

I know exactly what you mean by the scorching July heat. 1100 miles in that! My hat is off to you! 

Not the iron butt of some of you, but did 475 miles from Carlsbad, NM to Dallas, TX during the first week of August one year in 110-deg heat. Wouldn't recommend it. (Pulled into Carlsbad the night before and it was 118-deg on the bank signs.)

The year before last I worked all day (second week of July) and got a call from my mother at a little after 6PM and said that dad was sick and going to the emergency room.  I ran down to (south) Myrtle Beach from Northern VA (about 435 miles).  Took 5 hours and 55 minutes.  Got there just after midnight.  It seemed like the longest trip of my life.  It was hard to not get a ticket.  I hung at mostly 90 the whole time.  I ran thru a heavy thunder storm near Emporia, VA for about 30 miles - never even let off.  I was pretty much the only thing on the road.  The only cops I saw where in VA and just before I got to MB.  Very tense and mentally draining ride.

Did a 770 round trip, just because, in Colorado last year. Most of my day trips are ~500-700. Probably gonna pull an 'iron butt' ride in June, ~1050 or thereabouts.

I rode from Billings MT to Bremerton WA which is 868mi according to google maps.  It was mid October 2001 and just dumping snow the whole day.  This was day 4 of 4 coming from Virginia Beach on a naked Sv650.  I was a whipped pup when I got in.  Thankfully I've gotten a little smarter since then.  I've done longer days, but not tougher than that one.  I melted my bootheel trying to keep my feet warm on the exhaust.

1400 miles in 17 hours on a basket case 75 Moto Guzzi 850T in Aug 91. Port St. Lucie, FL to St. Peters, MO. Gas was under $1 when we left home and was $1.50 when we got to FL. We didn't know Saddam went into Kuwait. We even stopped for a while and had a few cold refreshments with a guy named Willie with the Dragons out of Detroit.
Then I rode from home to my son's in Norfolk in 16 hrs, the next day attended his wedding, went to dinner with the group, then hopped on the bike and went home via Bristol, VA then Deal's Gap. Left on Thursday, got home Sat. That was on the 97 Connie.

 The final leg coming home from the national rally in Frisco,CO in '08, Casey, IL to Cleveland, OH, not very far, maybe 400 miles, but mid-90's all the way home after the whole area just got inches of rain, humid is not the word, sauna like. Just our underwear under our coats and over pants, I would not recommend doing that again, not wearing clothes under our gear.

09 Fall COG Rally in Lake George. Only 675 miles, but it rained, then snowed and went from 55 to 25 in about 150 miles. 12 hrs. after leaving I made it home, temp was 23 deg. and still snowing. The only good thing was the wind didn't allow the snow to cover the roads.  But it did knock those temps down.
I think it took 3 days to recover from that days ride.   
RSA,
Greg

1135 miles in 21 hours. Culpeper, VA to Eureka Springs, AR. Not too bad a ride until the last hour. Dark, started raining, wrong turn onto a deserted backcountry road, no GPS. I tell you what; a little fatigued, having a tough time seeing through the rain and road-smeared face shield, not sure where the road was leading, and (swear to god) armadillos springing up into the air at the side of the road made me question my sanity a bit.

Got this for my efforts:

Sad to say but this happened in another lifetime. I had ridden to Gunnison, CO on my Yamaha SX650 -- a motorcyle that you could charitably say vibrated a little. And what do you do when you are young and stupid and staying at the location of Wasted State University -- a serious party school. Well, of course, you get stinking drunk! Not just inebriated but ... well there are no words.

The next day I had to ride back to Greeley, CO, about 8 hours, almost all two-lane riding. It was the longest day of my life -- I have never hurt so much. The only redeeming part of the day is that my riding buddy was an HD 883 butt destroyer.  We would ride until it hurt to much and that stop until that hurt too much and then ride again.

Ah, to be young again!!!

Done a Bun Burner Gold last fall, 1519 miles in 23 hours 32 minutes. What made it tough was instead of leaving at 6 am as planned we did not get going until 11 am. Then we ran into a traffic jam on the north side of Lake Ponchartrain. Taking up all of our banked time except 2 minutes. We never recovered from that set back and was only able to sleep for 30 minutes behind a warehouse in Blythesville, AR.

John

BBG, Lyons to T.W.O via Cheyenne on Sep 10, 2004 is up there.
Hauling my arse from Lyons to Bartlesville, OK (750+ miles) to pick up Barney (and a potential BBG) was up there too.
Most depressing was attempting my first Moonshine Lunch Run, and bagging a SS in the process. Blizzard conditions just east of Denver. If I'd left home an hour earlier, I would have missed all the snow.

Non motorcycle, my recent trip to Marshfield, MA. But I took three days. The return home was enjoyable though

Rick

Searched for over 2 years trying to find a mint condition 91 GSXR 1100 (had one in my youth), finally found one down in LA that popped up on CL. Bought a one way plane ticket from Portland to LA, got down there bought it and started my 1000+ mile journey back home, plan was to ride to the bay area on day one to spend the night at a buddies then finish the trek home day 2...
 
Got pulled over doing a buck ten'sh down the highway, cool CHP only wrote me up for 95 and said to slow down and sent me on my way. 
 

 
 
Made it to within about 60 miles of Sacramento and the bike died, turned out to be the carbs plugged because the bike had sat in a garage so long that eventually some crap broke loose... 
 
Had to call 911 and get towed to the nearest bike shop, $300 tow... 
 

 
 
Spent the night in some POS Motel 6 that had no resturant nor no food within walking distance, got a samich and 12 pack from gas station across the lot...
 

 
 
Next day rented a Uhaul from the local feed store and drove her home in the back the rest of the way, add $1k... 
 
 
 
Really sucked at the time but I still have that Gixxer and lover her even more... 
 

 
 

   May not qualify, but by far the worst day of my life on a bike was coming home from S-E Ohio ride on my XL 600 hit an  early fall COLD rain and it was the last time I did not have weather gear. I was reasonably sure that I would die before I got thru Columbus rush hour....when I had just thought....I'm almost there

     Mike

I would have to say the trip to Maine where we made it to Ithaca NY from OHIO in the pouring down rain........that really sucked bad!!!!!!